The 99 Best Movies of 1999, Ranked

The star of Bull Durham and Field of Dreams returns to the mound for one more affectionate ode to America’s pastime. You don’t need to know a splitter from a 98-mile-an-hour heater to appreciate the salty pathos Kevin Costner brings to Billy Chapel, an aging Detroit ace looking to close out his career with a perfect game — that is, if he can keep his mind from wandering to Kelly Preston’s dream-girl-who-got-away, introduced through flashbacks that lay out the bumpy course of their romance. Sam Raimi, the Evil Dead maverick calling the pitches, forgoes his usual demonic fastball in favor of a style as relaxed as a Sunday on the couch with a double header on the tube. It’s a right-down-the-middle Dad Movie — and a nice victory lap for an actor who always looks at home with his eyes on home plate. —A.A. Dowd

Fresh off her visually stunning, Tony-winning Broadway adaptation of The Lion King, director Julie Taymor attacked the big screen with an equally bold vision, turning one of Shakespeare’s least-loved tragedies into a striking, absurd extravaganza. Anthony Hopkins, at his most scene-chewing virtuosic, makes a meal out of Titus Andronicus, the mighty Roman general who returns home victorious after slaying the Goths, his impetuous execution of the eldest son of the defeated Goth regent Tamora (Jessica Lange) backfiring when she becomes Queen of Rome, setting the stage for a series of increasingly twisted reprisals between the two combatants. Written when the Bard was young and looking for a bloody, gruesome hit that would strike a chord with the masses, Titus Andronicus lacks the elegance of his later masterworks like Hamlet or King Lear. But Taymor’s visual flair, cheeky irreverence and inspired extravagance argue that it may be Shakespeare’s most shamelessly entertaining drama. In her impertinent, lavish retelling, revenge is a dish best served cold — and also with a bit of a wink. —T.G.

There had been screen adaptations of August Strindberg’s 1888 drama about the sexual tension between a Count’s daughter and her father’s personal valet both before and after director Mike Figgis (Leaving Las Vegas, The Loss of Sexual Innocence) gave us his interpretation, including a well-respected 2014 movie starring Colin Farrell and Jessica Chastain. But there’s something about this ’99 iteration, starring Saffron Burrows as the title character and Peter Mullan as the object of her fancy and her cruelty, that taps into the more feral aspects of the story’s master-and-servant dynamic. The handheld camerawork only ups the instability of the situation, making you feel as if everything will either explode or unravel at a moment’s notice. It’s proof that the play could still be a powder keg more than a century after the fact. —D.F.

The 1990s were a weird decade for Woody Allen. (We’re talking professionally — personally is a whole other discussion.) He made some of his biggest hits (Bullets Over Broadway, Mighty Aphrodite), one bona fide masterwork (Husbands and Wives), and a lot of miscellaneous debris. But he closed the 20th century out on a surprisingly high note, with this cross between a mockumentary about a fake jazz -guitar legend named Emmet Ray (Sean Penn) and an oddball rom-com. A contemporary of Django Reinhardt, Ray is talented jerk with big ideas; you wouldn’t think he’d fall for the mute laundress (Samantha Morton) he meets at the beach, and yet they make for a cute couple. It’s only later that he realizes she’ll be the one who got away, and that heartbreak makes for good artistic inspiration. And while Penn provides the proper amount of lowdown, it’s Morton’s absolutely sweet, silent-comedy take on his object of affection that truly makes the movie work. —D.F.

Oscar Wilde’s 19th century play gets a late-20th century Miramax makeover, complete with Masterpiece Theater-worthy production design, a Brit cast who excelled in adding extra bite to Wilde’s witty bon mots (lookin’ at you, Rupert Everett and Jeremy Northam) and a host of late 1990s stars (Julianne Moore, Minnie Driver, and a positively babyfaced Cate Blanchett). Everett’s Lord Goring, “the idlest man in London,” wants nothing more than to traipse around the city and indulge in his every lascivious whim. Then a blast from his past, Mrs. Cheverly (Moore), shows up, with political maneuvers, blackmail and revenge on her mind. “Are you not just a little bit please to see me?” she asks Goring. “Possibly even less than that,” he replies. If you just tittered a little reading this as you took a sip of Earl Grey tea, then this adaptation is most certainly for you. —D.F.

Joe (David Strathairn), a small-town Alaska handyman, is trying to live down a tragic mistake from his past. He falls for a singer, Donna (Mary Elizabeth Mastrantonio), who’s dealing with her own emotional baggage. The limbo of the title refers not just to this frozen hinterland but to the hesitant main characters who risk giving love a try, only to have their lives upended by a shock twist involving Joe’s brother. As always, filmmaker John Sayles has a sharp eye for the customs and rhythms of the world he chronicles, which give this movie a richness that extends to the weathered, weary performances from Strathairn and Mastrantonio. As for the film’s divisive ending, it speaks eloquently to the anxiety of the unknowns that await us all — from day to day, we’re never sure if we’re living in a gentle comedy or a dark thriller. —T.G.

Some advice to filmmakers hoping to turn classic kids-lit into memorable movies: Get Michael J. Fox to voice your animated, anthropomorphized heroes. The former Marty McFly is the definitely the secret sauce that makes Rob Minkoff’s take on E.B. White’s famous book — about a tiny white mouse who is adopted by humans, and must eventually choose between his biological rodent parents and his new Homo sapien family — work way better than you’d expect it to. There’s an innocence and joy he brings to his miniature CGI hero, especially in scenes with his initially reluctant new brother Jonathan Lipnicki, as well as a pathos to lines such as “I feel an empty space inside me, and I just wanna know what was there before.” The rest of the cast is nothing to sneeze at, of course — this breezy, enjoyable kids’ flick is the answer to the trivia question, “What movies features the talents of Geena Davis, Hugh Laurie, Nathan Lane, Chazz Palminteri, Dabney Coleman, Steve Zahn, Jennifer Tilly, Julia Sweeney, Brian Doyle-Murray, Estelle Getty, David Alan Grier, Bruno Kirby and comic legend Stan Freberg?” But it’s Fox who gives this “little” movie a big heart. —D.F.

Starting with its extended, single-shot opening — which immediately connects the dots between the theater space, the politically active artist and trod-upon everyday people — writer-director Tim Robbins’ boisterous drama shows that its willing to risk wearing both its ambitions and its intentions all over its sleeve. Combining the behind-the-scenes workings of the Federal Theater Program, Orson Welles attempt to stage the lefty musical The Cradle Will Rock for the FTP, and Nelson Rockefeller’s commissioning of Diego Rivera to paint a mural in the lobby of Rockfeller Center (along with a few other burbling subplots), this look back at the complicated relationship between commerce, the arts and agitprop is itself a work of agitprop, sounding the alarm about what happens when creative types cozy up to corporate bigwigs. Robbins raided his Rolodex for the fit-to-burst ensemble cast, which includes Bill Murray, Cherry Jones, Hank Azaria, Emily Watson, Susan Sarandon, John Turturro, Paul Giamatti, Vanessa Redgrave, Rubén Blades, two Cusacks (John and John) and both members of Tenacious D. And while no one would accuse it of being anything less than unganily, it’s the sort of overly sincere big swing we could use more of right now. —D.F.

“Just what the hell did you do to the sharks!?” asks Samuel L. Jackson, with the same booming outrage he’d later reserve for motherfucking snakes on a motherfucking plane. The pseudoscientific answer to his question might have put a toothy grin on Michael Crichton’s face. Crossbreeding Jaws with Jurassic Park, junk-cinema maestro Renny Harlin unleashes a school of brainy maneaters — some brought to life via the prehistoric wonder of animatronics — on a water-logged research facility. The improbabilities mount faster than the bodies. Is that Michael Rapaport as a brilliant scientist? Did that shark just try to cook LL Cool J in an oven? What gives this glorified B-movie some real bite is the merciless glee in which it chows down on its overqualified cast. No role is so big that it guarantees survival. No monologue is so inspirational that it can’t be ferociously cut short. —A.A.D.

Tim Burton applies his Grand Guignol mall-goth vibes to Washington Irving’s short story, about a hapless man named Ichabod Crane who has a first-hand encounter with local urban legend “the Headless Horseman.” This time around, Crane gets promoted from schoolteacher to a New York City police constable sent upstate to investigate a series of mysterious decapitations; he also goes from the gangly, lanky figure of the Disney cartoon to resembling Johnny Depp, who pairs well with Christina Ricci’s pale-skinned heiress Katrina Van Tassel. The vibe here channels a lot of vintage Hammer horror and the 1960s Edgar Allan Poe cycle of films from American International Pictures, and while the overal pedigree is strong (Francis Ford Coppola is an executive producer, Seven‘s Andrew Kevin Walker wrote the screenplay and god-tier cinematographer Emmanuel “Chivo” Lubezki shot it), it’s very much a Burton film from start to finish. —D.F.

In the West Virginia town of Coalwood circa 1957, you either work in the mines or you teach kids who will eventually grow up to work in the mines. You don’t usually go on to become a rocket scientist. But young Homer Hickam — look how baby-faced you were, Jake Gyllenhaal! — watches the recently launched Sputnik go blazing through the night sky, he suddenly becomes obsessed with building his own rocket. His friends and the school brainiac help him build miniature prototypes. His working-class father (Chris Cooper, in is his other big toxic-repressed-male role of ’99) disapproves of such foolishness. A kindly teacher (Laura Dern) thinks this project will not only take him to the national science fair, but possibly be his ticket to a brighter future. Director Joe Johnston also made The Rocketeer, so he’s clearly down for the cause as well. A lovely biopic about a real-life dreamer — Hickam would becoime a real-life aerospace engineer at NASA — which adds a nice bit of grit to its Norman Rockwell-esque Americana. —D.F.

Before she was Carmela Soprano, Edie Falco gave us the title character in Eric Mendelsohn’s black-and-white indie gem: an aspiring actor with a unflappably upbeat attitude. She’s on her way to make it big in the moving pictures in Hollywood, USA, i.e. the same Tinseltown that just chewed up and spit out her old high school crush, a would-be filmmaker named David (Aaron Harnick). Meanwhile, both of their respective sets of parents — including the great Madeline Kahn, in her final film role — seem to be stuck living lives of quiet desperation and an extremely symbolic eclipse is enveloping their hometown of Babylon, Long Island, in darkness. It’s a great example of how the New York wing of late-1990s independent filmmakers were combining the wry DIY aesthetic of Hal Hartley, etc., with the whimsical humanism of their Park City cohorts. That Mendelsohn’s character study won him the Best Director award at that year’s Sundance isn’t the least bit shocking. —D.F.

Ralph Fiennes had already demonstrated he was an expert at showing simmering passions coming to a spilling-over boil courtesy of The English Patient three years earlier — and for this adaptation of Graham Greene’s novel about jealousy, adultery, and Catholic guilt, he happily turns the temperature up even further. Tracing an on-again, off-again obsession intertwined with WWII, this look at the fallout of a tempestuous affair between Fiennes’ novelist and Julianne Moore — who’s the wife of an old acquaintance — balances prestigious stiff-upper-lip period drama with explicit scenes of two lovers in a mutual state of heat. Indeed, there may not be a more dizzying, swoon-worthy moment in either actor’s filmography (or director Neil Jordan’s back catalog) than the couple walking out a restaurant after a faux-polite conversation and suddenly kissing each other compulsively under a raincoat. And as in Greene’s novel, there are matters of faith that complicate their infidelity, adding a whole other layer to their unbridled lust during wartime. —D.F.

The tagline for Ang Lee’s stab at a Seventies-style revisionist Western set during the Civil War was that soldiers “didn’t fight for the Blue and the Gray… they fought for their friends and their family.” It helps set the context for his unusual, highly visceral take on the War of Southern Aggression, given that we’re asked to ride with pro-Confederate guerrillas like Quantrill’s Raiders and Missouri’s “Bushwhackers” — any recognizable, binary notions of good-vs.-evil and us-vs.-them get muddied from the moment the movie hits the ground running. The scenes of battle aren’t designed to be rah-rah rousing, and in following Tobey Maguire’s young, German immigrant (who takes up the Confederate cause out of revenge) and Jeffrey Wright’s former slave as they seek shelter in between raids, you get to see their more personal conflict play out off the battlefield as well. Kudos go to singer Jewel Kilcher as well, who makes the most of her role as a widow who crosses their path. In a year filled with so many extraordinary movies across the board, it was easy for something like this to fall through the cracks. Now that Lee’s longer “director’s cut” is out in the world, this is one of those ’99 movies ripe for rediscovery. —D.F.

Who better to tackle Herman Melville’s 1852 novel Pierre; or, the Ambiguities — a “curiosity of literature” filled with sex, subversiveness, and a warped spirituality that had critics calling its creator immoral — than a filmmaker who understood what it was like to push envelopes and piss off tastemakers? Like the Moby Dick author, Leos Carax was coming off a magnum opus (1991’s The Lovers on the Bridge), and the French writer-director’s adaptation manages to tap into his romanticism (capital and lowercase R versions) and a palpable sense of rage. Pierre (Guillaume Depardieu, a.k.a. Gérard’s kid) has a doting mom (Catherine Deneuve), a fiancé (Delphine Chuillot), and a successful novel under his belt. Then, one night in the forest, he encounters Isabelle (Yekaterina Golubeva), and falls so head-over-heels for her that not even the disclosure that she’s his half-sister can stop them from an amour most fou. What follows is extremely un-simulated sex, a waterfall of blood, some incredible Scott Walker songs, and the sense that you’ve either witnessed the demented work of a genius or the work of a demented genius. We favor the second one. —D.F.

Based on Denis Johnson’s short story collection, this stark, starling indie film follows FH (Billy Crudup), a junkie flailing through the 1970s, eventually clawing his way to recovery. Premiering at Telluride in 1999 and released in the States the following year, the movie is raw but funny, seeing in its shambling protagonist the sort of idiosyncratic antihero who wouldn’t have been out of place during the New Hollywood era. The supporting cast features a who’s who of dazzling character actors and rising stars, including Samantha Morton, Denis Leary, Jack Black, and Michael Shannon. But the focus is always on how heroin’s promise of transcendence is undermined by the ugliness of all it takes from its luckless users. —T.G.

What, you thought Tony Soprano had a lock on the whole Mafia-boss-goes-to-therapy racket? This Robert De Niro and Billy Crystal comedy, about a Cosa Nostra capo getting in touch with his feelings thanks to a reluctant, neurotic shrink — we’ll let you guess which actor portrays which character — hit theaters a few months after HBO’s flagship series premiered. But the idea had been percolating way before Tony started freaking out over a family of ducks, and plays the idea of a tough-guy gangster not for pathos but strictly for laughs. It helps that the legendary Harold Ramis is calling the shots (he also contributed to the script alongside Kenneth Lonergan and The Larry Sanders Show writer Peter Tolan), and that De Niro also seems to be having a blast both channeling and making fun of his past Mob-movie turns. To paraphrase the man himself: You’re good, you. You are very good, Analyze This. Read it in a De Niro voice and it sounds better. —D.F.

Following a prolific period in the 1980s when he produced several classics in quick succession, including Castle in the Sky and My Neighbor Totoro, legendary Japanese animator Hayao Miyazaki went five years between 1992’s Porco Rosso and this epic fantasy tale, and you can feel the effort and care in every frame of the film, which made his allegiance to the natural world as overt and impassioned as any in his remarkable, environmentalist oeuvre. Set in medieval Japan, Princess Mononoke chronicles a growing conflict between the human world and the spirits who protect the forest — in the middle of that feud is a noble prince, Ashitaka, who’s on a journey to rid himself of a terrible curse. This beautifully hand-drawn drama — the lengthiest of Miyazaki’s films — took two years after its Japanese premiere to finally reach the United States, where it was released by Miramax’s Harvey Weinstein, who dared to suggest trims to the master. Thankfully, Miyazaki wasn’t having it. “I did go to New York to meet this man, this Harvey Weinstein,” he recalled in 2005, “and I was bombarded with this aggressive attack, all these demands for cuts.” With great pride, Miyazaki added, “I defeated him.” —T.G.

George Festrunk and Mr. Robinson, together at last! Frank Oz’s sublimely silly showbiz satire casts Steve Martin as a modern Ed Wood shooting a Z-grade science fiction opus guerilla-style, with a movie star who doesn’t even know he’s in the movie. Eddie Murphy is that star, a vain, flaky A-lister being clandestinely filmed (read: stalked) by the amateur production. Murphy also plays the actor’s nerdy twin brother — an inspired bit of dual casting that allows this gifted chameleon both to spoof his own celebrity and offer another gentle caricature of misfit sensitivity, à la The Nutty Professor. Oz clowns on everything from the insidious influence of Scientology to the sexual quid pro quo driving so much casting without ever stooping to mean-spiritedness. That’s the joy of his farce: It looks at the cynical truth of Hollywood through widely innocent eyes, all while colliding the unexpectedly simpatico shtick of two comedy legends. —A.A.D.

Like every 007 before and after him, Pierce Brosnan has played a few debonair ladykillers outside of the tuxedo, too. A mere three months shy of reprising the role of James Bond in The World is Not Enough (see above), he unofficially refined it, deviously tweaking his preppy charisma to portray a suave art thief in this effortlessly stylish remake of a 1968 Steve McQueen caper. Rene Russo matches Brosnan step for step as the smart, sexy insurance investigator on his tail; the two dance wittily around their mutual attraction, before surrendering to it during the kind of steamy Hollywood love scene now as rare as an original Monet. Most actual Bond movies would kill for their chemistry — or for a scene as nimble and playful as the closing heist, which Die Hard director John McTiernan sets to the jaunty, timeless accompaniment of Nina Simone’s “Sinnerman.” —A.A.D.

The Nineties loved the aesthetics of the 1960s. (Remember that ever-present hippie smiley face?) But maybe no film did kitschy Sixties aesthetics better than Andrew Fleming’s delightful but also delicious political comedy. Kirsten Dunst and Michelle Williams are two goofy girls who accidentally stumble upon the Watergate break-in. They soon become persons of interest for both Richard Nixon himself (a perfect Dan Hedaya) and Woodward and Bernstein (Will Ferrell and Bruce McCulloch), all while maintaining their glorious cluelessness. Tricky Dick never stood a chance. —Esther Zuckerman

This love letter to indie-rock heroes Fugazi was a lot like the band’s music: uncompromising and intense, at times a bit tedious but ultimately uniquely rewarding. Dispensing with crutches like narration or contextual hand-holding, filmmaker Jem Cohen, a trusted friend of the band for years, deep-dives into a impressionistic blur of live and studio footage, as well as interviews with the band and their fans (including an adorable clip of singer-guitarists Ian McKaye and Guy Picciotto on a cable access show hosted by a teenage girl). The performance clips are often spellbinding, including an instantly legendary moment from a show in a high school gym where Picciotto sings suspended upside down from a basketball hoop. And the band’s unparalleled integrity and determination come through in every grainy, disjointed, process-obsessed, passion-filled minute. —J.D.

Anthony Hopkins isn’t the only stocky Brit with a deranged chef on his resume of Nineties roles. To his alphabetical right stands Cockney tough guy Bob Hoskins, who brings a rather subtle, subdued menace to this haunting thriller about an Irish teenager who goes looking for her lost love and instead falls into the clutches of a seemingly kindly cook with some dangerously unresolved mommy issues. Just don’t expect cheap serial-killer thrills — not with Atom Egoyan behind the camera and keyboard. The Exotica director fractures his William Trevor source material into another puzzle-box tragedy of childhood trauma, predatory men, and a past that keeps bleeding (via a trickle of flashbacks) into the present. The sound design — an overlapping din of voices, industrial noise, and staccato violin — suggests the room tone of a disturbed mind. But it’s the English bulldog in the lead who really opens a window into that space, letting us see the pitiable boy behind the madman. —A.A.D.

There’s a part of us that gets giddy at the idea that, having thrilled to Kate Winslet’s performance in Titanic, a gaggle of recently converted Winslet-ites then flocked to see this truly cracked psychodrama, about a young Australian woman who falls under the spell of a cultlike leader while in India. Once she’s eventually cajoled back to her hometown in Sydney, Winslet’s character is sequestered with an American (Harvey Keitel) who’s an expert in deprogramming brainwashed ex-cult members. Let’s just say that neither of them plans on giving up without a fight, and that the lines of what is and isn’t acceptable social behavior gets severely blurred in Jane Campion’s underrated take on spiritual voids and sexual power plays. Had Winslet’s previous movie not already been named Hideous Kinky, that title would have been equally appropriate here. —D.F.

Most tales of how we tamed the wild, wild West leave out some of the more grisly footnotes — luckily, director Antonia Bird’s berserk frontier-horror parable is more than happy to fill in the gaps. A traumatized army lieutenant (Guy Pearce) is transferred to a remote outpost in California after the Mexican-American War left him “unfit” for normal duty. He’s barely settled in with his fellow misfits and scallywags when a mysterious Scottish drifter (Robert Carlyle) shows up on their doorstep. It seems he was a member of a settlers’ party heading west through the Sierra Nevada, and after they became stranded without food for several weeks… let’s just say that desperate times begat desperate measures. The soldiers accompany him to the scene of the crime to rescue his fellow survivors, at which point they discover that both old habits and new appetites are hard to shake off. A singular mix of revisionist Western, stalker flick, survivalist thriller and, yes, even wackadoo comedy, Ravenous distinguished itself as one of the sickest jokes of 1999 — a reminder that America’s origin story includes cowards, cannibals, and good old-fashioned psychopaths. —D.F.

In 1975, Bob Dylan released “Hurricane,” a song that decried the false conviction of middleweight boxer Rubin “Hurricane” Carter, who was given lifetime sentences for the 1966 killing of three people in a New Jersey bar. Director Norman Jewison chronicles his story in a stirring biopic that is part sports film and part courtroom drama, starring Denzel Washington, masterful as usual playing a man lethal in the ring but powerless in the face of a cruel legal system. The protest anthem helped keep Carter’s case alive in the culture years after he was initially incarcerated (he eventually had his conviction overturned in 1985). Yet the movie aided in putting a human face to this torn-from-the headlines story of racism and injustice, as well as reminding audiences of the work that activist groups (like the one led by Liev Schreiber in the film) do to free the innocent from prison. —T.G.